Transition metal-catalyzed directed C(sp3)–H functionalization of saturated heterocycles
File(s)
Accepted version
Author(s)
Antermite, Daniele
Bull, James
Type
Journal Article
Abstract
Synthetic methods that can readily access saturated heterocycles with different substitution patterns and with control of stereo- and regiochemistry are of huge potential value in the development of new medicinal compounds. Directed C–H functionalization of simple and commercially available precursors offers the potential to prepare diverse collections of such valuable compounds that can probe the different available exit vectors from a ring system. Nonetheless, the presence of the Lewis basic heteroatoms makes this a significant challenge. This review covers recent advances in the catalytic C–H functionalization of saturated heterocycles, with a view to different heterocycles (N, O, S), substitution patterns and transformations.
1. Introduction
2 alpha-C–H Functionalization with directing group on nitrogen
3 C–H Functionalization at unactivated C(3), C(4) and C(5) positions
3.1 C–H Functionalization at C(3) with directing groups at C(2)
3.2 C–H Functionalization at C(3), C(4) and C(5): Directing groups at C(4) and C(3)
4 Transannular C–H functionalization
5 Conclusion
1. Introduction
2 alpha-C–H Functionalization with directing group on nitrogen
3 C–H Functionalization at unactivated C(3), C(4) and C(5) positions
3.1 C–H Functionalization at C(3) with directing groups at C(2)
3.2 C–H Functionalization at C(3), C(4) and C(5): Directing groups at C(4) and C(3)
4 Transannular C–H functionalization
5 Conclusion
Date Issued
2019-09-01
Date Acceptance
2019-04-03
Citation
Synthesis: journal of synthetic organic chemistry, 2019, 51 (17), pp.3171-3204
ISSN
0039-7881
Publisher
Thieme Publishing
Start Page
3171
End Page
3204
Journal / Book Title
Synthesis: journal of synthetic organic chemistry
Volume
51
Issue
17
Sponsor
The Royal Society
The Royal Society
The Royal Society
Identifier
https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1611822
Grant Number
UF140161
RG150444
RGF\EA\180031
Subjects
Science & Technology
Physical Sciences
Chemistry, Organic
Chemistry
C-H functionalization
saturated heterocycles
transition metal catalysis
stereoselectivity
regioselectivity
C-H BOND
ALPHA-AMINO-ACIDS
UNACTIVATED C(SP(3))-H
STEREOSELECTIVE-SYNTHESIS
ALIPHATIC-AMINES
DIRECT ARYLATION
NITROGEN ATOM
REMOTE FUNCTIONALIZATION
INTRAMOLECULAR AMINATION
PHOTOREDOX CATALYSIS
Organic Chemistry
0305 Organic Chemistry
0301 Analytical Chemistry
Publication Status
Published
Date Publish Online
2019-06-17